Literature DB >> 15606118

Domino reactions that combine an azido-Schmidt ring expansion with the Diels-Alder reaction.

Yibin Zeng1, D Srinivasa Reddy, Erin Hirt, Jeffrey Aubé.   

Abstract

[reaction: see text] The combination of the intramolecular Schmidt reaction with the Diels-Alder reaction provides expedient access to a variety of heterocycles. Two different modes of reaction planning are presented. In one, the azide and ketone moieties necessary for the intramolecular Schmidt reaction originate on different molecules that are reacted and subsequently undergo a ring-adjustment step. Alternatively, an azido ketone can be used provided the ketone is deactivated by its presence in an enone.

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Year:  2004        PMID: 15606118     DOI: 10.1021/ol047809r

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  13 in total

1.  A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.

Authors:  Angelica M Meyer; Christopher E Katz; Sze-Wan Li; David Vander Velde; Jeffrey Aubé
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy.

Authors:  Alan Rolfe; Paul R Hanson
Journal:  Tetrahedron Lett       Date:  2009-12-16       Impact factor: 2.415

3.  Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands.

Authors:  Kevin J Frankowski; Vincent Setola; Jon M Evans; Ben Neuenswander; Bryan L Roth; Jeffrey Aubé
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-28       Impact factor: 11.205

4.  Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

Authors:  Pilho Kim; Clifton E Barry; Cynthia S Dowd
Journal:  Tetrahedron Lett       Date:  2006-05-15       Impact factor: 2.415

5.  Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid.

Authors:  Alan Rolfe; Kyle Young; Paul R Hanson
Journal:  European J Org Chem       Date:  2008

6.  Efficient access to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes.

Authors:  Michael C McLeod; Jeffrey Aubé
Journal:  Tetrahedron       Date:  2016-06-30       Impact factor: 2.457

7.  Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.

Authors:  Kevin J Frankowski; Benjamin Neuenswander; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2008-08-13

8.  One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions.

Authors:  Chan Woo Huh; Gagandeep K Somal; Christopher E Katz; Huaxing Pei; Yibin Zeng; Justin T Douglas; Jeffrey Aubé
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  One-pot, three-component, domino Heck-aza-Michael approach to libraries of functionalized 1,1-dioxido-1,2-benzisothiazoline-3-acetic acids.

Authors:  Alan Rolfe; Kyle Young; Kelly Volp; Frank Schoenen; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2009 Jul-Aug

10.  Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.

Authors:  Yu-hong Lam; Paul Ha-Yeon Cheong; José M Blasco Mata; Steven J Stanway; Véronique Gouverneur; K N Houk
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

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